Acetic Acid → 2-(4-Nitrophenyl)butyric acid

Participants

Reaction Conditions

Reaction Steps

A solution of 33.9 g of 2-phenylbutyric acid in 340 ml of concentrated sulfuric acid was cooled to -10° C. with stirring. To this solution was added, dropwise, a mixture of 39.4 ml of 70% nitric acid and 170 ml of acetic acid at such a rate that the temperature was maintained below 0° C. The mixture was then warmed to 20° C. over a period of 1 hour and poured into ice water. The off-white solid which formed was separated by filtration, washed with ice water and sucked as dry as possible on the filter. The resultant solid was dissolved in chloroform, a water layer was separated, and the chloroform layer was dried over magnesium sulfate. The solvent was removed under reduced pressure to give a crude solid which was recrystallized from a mixture of hot toluene/hexane to give 2-(4-nitrophenyl)butyric acid.

Provenance & Evidence